2-[2-(Morpholin-4-yl)ethyl]-2H-indazol-5-amine → N-tert-Butyl-3-{2-[2-(2-morpholin-4-yl-ethyl)-2H-indazol-6-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide

HRID 1262380Notes

Reaction equation

HRID 1262380 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:25]1([CH2:31][CH2:32][N:33]2[CH:41]=[C:40]3[C:35]([CH:36]=[C:37]([NH2:42])[CH:38]=[CH:39]3)=[N:34]2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.N1(CCN2C=C3C(C=CC(N)=C3)=N2)CCOCC1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:42][C:37]4[CH:38]=[CH:39][C:40]5[C:35]([CH:36]=4)=[N:34][N:33]([CH2:32][CH2:31][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:41]=5)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 574161312-[2-(Morpholin-4-yl)ethyl]-2H-indazol-5-amineHCID 574161322-[2-(Morpholin-4-yl)ethyl]-2H-indazol-6-amineHCID 178449976HCID 178449976, compound

Product 1

HCID 46851038N-tert-Butyl-3-{2-[2-(2-morpholin-4-yl-ethyl)-2H-indazol-6-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide

Procedure

Following the procedure of Example 1315, N-tert-butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (114 mg, 0.330 mmol) was coupled in parallel fashion to 2-(2-morpholin-4-yl-ethyl)-2H-indazol-6-ylamine (57 mg, 0.23 mmol) and 2-(2-morpholin-4-yl-ethyl)-2H-indazol-5-ylamine (57 mg, 0.23 mmol). Products were purified by RP pHPLC as described in Example 1291c. Yield of TFA salt: 71 mg (62%); LC/MS: 575 (M+H); HPLC: 97% pure, RT=2.73 min; 1H NMR: (DMSO, δ) 9.68 (s, 1H), 9.08 (s, 1H), 8.73 (d, J=7.9, 1H), 8.42 (s, 1H), 8.38 (s, 1H), 8.19 (s, 1H), 7.87 (d, J=7.8, 1H), 7.77 (t, J=7.7, 1H), 7.72 (s, 1H), 7.69 (d, J=9.0, 1H), 7.36 (d, J=9.0, 1H), 7.25 (d, J=4.8, 1H), 7.04 (d, J=4.8, 1H), 4.85 (t, J=5.7, 2H), 3.85 (m, 4H), 3.80 (m, 2H), 3.30 (m, 4H), 1.13 (s, 9H).

Workup

  1. customProducts were purified by RP pHPLC

Sources & evidence

ORD record
ord-5fa6569c340347ce834a536254fb4368
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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